Paruch E, Ciunik Z, Nawrot J, Wawrzeńczyk C
Department of Chemistry, Agricultural University, ul. Norwida 25, 50-375 Wroclaw, Poland.
J Agric Food Chem. 2000 Oct;48(10):4973-7. doi: 10.1021/jf991307o.
Starting from (+)- and (-)-perillyl alcohols, via Claisen rearrangement and iodolactonization, four enantiomeric pairs of gamma-lactones were obtained. The structures of compounds were established by both spectroscopic and crystallographic methods. The lactones were tested for antifeeding activity toward grain storage pests-the granary weevil beetle (Sitophilus granarius L.), the khapra beetle (Trogoderma granarium Ev.), and the confused flour beetle (Tribolium confusum Duv.). The results of the tests proved that two compounds, (1R,4R, 6R)-(-)-4-(1-methylethenyl)-9-oxabicyclo[4.3.0]nonan-8-one (8a) and its enantiomer (8b), are very active antifeedants against all of the above tested species. The lactone 8b is also active against the peach-potato aphid (Myzus persicae Sulz.). The activity depends on the absolute configurations of compound chiral centers. Additionally, the lactones 8a and 8b are characterized by interesting fragrances.
从（+）-和（-）-紫苏醇出发，经克莱森重排和碘内酯化反应，得到了四对对映体γ-内酯。通过光谱法和晶体学方法确定了化合物的结构。对这些内酯对储粮害虫——谷象（Sitophilus granarius L.）、谷斑皮蠹（Trogoderma granarium Ev.）和赤拟谷盗（Tribolium confusum Duv.）的拒食活性进行了测试。测试结果证明，两种化合物，即（1R,4R,6R）-（-）-4-（1-甲基乙烯基）-9-氧杂双环[4.3.0]壬烷-8-酮（8a）及其对映体（8b），对上述所有测试物种都是非常有效的拒食剂。内酯8b对桃蚜（Myzus persicae Sulz.）也有活性。活性取决于化合物手性中心的绝对构型。此外，内酯8a和8b具有有趣的香味。
